The goal of this research is to discover and develop practical methods for the asymmetric oxidation of organic compounds. For the present we have chosen to concentrate on asymmetric oxidations of olefins, since no other functional group is as susceptible to such a wide variety of useful oxidative transformations. Epoxidation, the single most important oxidative process for olefins, will continue to receive special attention. Our main approach is to devise chiral metal catalysts and thereby realize high enantioselectivities in the same manner that enzymes do. This requires the synthesis of special chiral ligands for the metals (e.g. titanium, vanadium, osmium, and selenium) which are active as oxidation catalysts. Oxidants which require a stoichiometric amount of a chiral reagent will also be explored. For example, we have recently seen up to 90% enantiomeric excess in the vicinal diols produced upon reaction of osmium tetroxide with olefins in the presence of an equivalent of a chiral alkaloid derivative. Another discovery from the present grant period is a new class of exceedingly selective, metal-catalyzed rearrangements of epoxyalcohols. This lead will be pursued since it significantly expands the utility of the chiral epoxyalcohols which can be prepared by asymmetric epoxidation of the corresponding allylic alcohols.